Sodium Hydroxide → HCID 86740850, compound

Participants

Reaction Steps

Ethyl(2-hexyl)but-2-enoate (12 g, 0.06M) in methanol (150 ml) was treated with sodium hydroxide (15 g, 0.375M) in water (100 ml) under reflux for 6 hours. The solvents were then removed in vacuo and the residue taken up in water and extracted with dichloromethane. The aqueous phase was separated, acidified to pH1 with concentrated hydrochloric acid and extracted with dichloromethane. The extract was dried over sodium sulphate and concentrated in vacuo to an oil which was distilled in vacuo to afford E and Z (2-hexyl)but-2-enoic acid (10.1 g, 0.06M) as the main fraction (b.p. 100°-110° C. at 0.5 mm Hg) (Found: C, 68.2; H, 10.4. C10H18O2 +0.5 H2O requires: C,68.5; H, 9.7%); δ(CDCl3) 0.88 (3H, m, CH3); 1.3 (8H, m, (CH2)4); 1.84 and 2.04 (3H, each m, each CH3CH); 2.32 (2H, t, J=8 Hz, CH2) 6.14 and 6.94 (1H, each q, each J=8 Hz, CH).

Provenance & Evidence